Multistate Photoswitches: Macrocyclic Dihydroazulene/Azobenzene Conjugates

Autor:	Kurt V. Mikkelsen, Anders B. Skov, Alexandru Vlasceanu, Mogens Brøndsted Nielsen, Mads Koerstz
Rok vydání:	2018
Předmět:	Materials science 010405 organic chemistry General Chemistry General Medicine 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Photochromism chemistry.chemical_compound Crystallography Azobenzene chemistry Covalent bond Molecule Isomerization Conjugate
Zdroj:	Angewandte Chemie. 130:6177-6180
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201712942
Popis:	Molecules comprised of three covalently linked bi-stable switches can exist in states described by a combination of binary numbers, one for each individual switch: ⟨000⟩, ⟨001⟩, etc. Here we have linked three photo-/thermoswitches together in a rigid macrocyclic structure, one azobenzene (bit no 1) and two dihydroazulenes (DHAs; bits no 2 and 3) and demonstrate how electronic interactions and unfavorable strain in some states can be used to control the speed by which a certain state is reached. More specifically, upon irradiation of state ⟨000⟩, the AZB isomerizes from trans to cis and the two DHAs to vinylheptafulvenes (VHFs), generating ⟨111⟩. The thermal VHF-to-DHA back-reactions from this state also occur stepwise and can be accelerated by photo-induced AZB cis-to-trans conversion, proceeding via ⟨011⟩ to ultimately furnish ⟨000⟩. Overall, the accessibility to a specific state of one bit was found to depend on the states of its neighboring bits.
Databáze:	OpenAIRE
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